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Winsted, CT 55+ active adult communities & homes for sale

78 communities near Winsted

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3.6 rating (7 reviews) Heritage Village
$100Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
The Village at Oxford Gre...
$600Ks - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
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Questions? Call us: (860) 909-8066
Rivington
$400Ks - $800Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
The Retreat at Carmel
$400Ks - $700Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Fairview at Oxford Greens
$600Ks - $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Regency at Woodbridge
$600Ks - $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Regency at Fishkill
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Spring Lake Village
$200Ks - $300Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
South Pond Village
$200Ks - $400Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
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The Village at Whispering...
$400Ks
The Village at Whispering...Rotterdam, NY
New Construction | 55+ age-restricted | Built 2025 - present | 85 homes
5 rating (1 reviews) Newtown Woods
$400Ks - $500Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
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Granite Woods
$600Ks - $700Ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Bartlett Hill
$500Ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Evergreen
$500Ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Baldwin Station
$400Ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Liberty at Newtown
$300Ks - $400Ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Gardens of Wilbraham
$500Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
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5 rating (1 reviews) Paris Square
$400Ks - $700Ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Glassbury Court at Cold S...
$500Ks - $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Glassbury Court at Hunter...
$500Ks - $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Billingsgate
$400Ks - $600Ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Boulder Brook
$200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Gloria Commons
$400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Hopmeadow Place
$200Ks - $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Long Hill Village
$300Ks - $400Ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Oak Meadow Estates
$400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Park Glen
$600Ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
RiverBend Estates
$400Ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Summer Wind Estates
$300Ks - $400Ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
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Questions? Call us: (860) 909-8066
The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Regency Meadows
$500Ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Bidwell Village
$300Ks - $400Ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Cobblestone Court
$400Ks - $500Ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Forest Mews
$300Ks - $400Ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
1...2
New Heritage Village 745 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$644,900

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

445 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New Jefferson Village 50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$475,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
New Rivington 1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681..., Danbury, CT 06810
$899,900

3 beds

|

3 baths

|

2,596 sq ft

|

Condo

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681...
Community: Rivington
New Fairview at Oxford Greens 909 TILLINGHAST DR # 909, OXFORD, CT, 06..., Oxford, CT 06478
$699,000

2 beds

|

3 baths

|

2,239 sq ft

|

Condo

909 TILLINGHAST DR # 909, OXFORD, CT, 06...
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
New The Village at Oxford Greens 909 TILLINGHAST DR # 909, OXFORD, CT, 06..., Oxford, CT 06478
$699,000

2 beds

|

3 baths

|

2,239 sq ft

|

Condo

909 TILLINGHAST DR # 909, OXFORD, CT, 06...
New Heritage Village 968 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Chatfield Farms 9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403
$515,000

2 beds

|

3 baths

|

1,700 sq ft

|

Condo

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0...
Community: Chatfield Farms
Jefferson Village 53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$439,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Sonoma Woods 60 SONOMA LN # 60, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$549,900

2 beds

|

3 baths

|

2,054 sq ft

|

Condo

60 SONOMA LN # 60, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Hills 339 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$500,000

2 beds

|

3 baths

|

1,550 sq ft

|

Condo

339 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
South Pond Village 162 THISTLE POND DR # 162, BLOOMFIELD, C..., Bloomfield, CT 06002
$395,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

162 THISTLE POND DR # 162, BLOOMFIELD, C...
Community: South Pond Village
Heritage Hills 882 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

3 baths

|

1,666 sq ft

|

Condo

882 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
The Retreat at Carmel 18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512
$749,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

18 WHEELER CT, CARMEL, NY, 10512
The Village at Oxford Greens 117 COUNTRY CLUB DR # 117, OXFORD, CT, 0..., Oxford, CT 06478
$649,900

3 beds

|

3 baths

|

2,666 sq ft

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0...
Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Hills 578 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$450,000

1 beds

|

2 baths

|

967 sq ft

|

Condo

578 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
The Village at Oxford Greens 301 FAIRWAY DR # 301, OXFORD, CT, 06478, Oxford, CT 06478
$619,000

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

301 FAIRWAY DR # 301, OXFORD, CT, 06478
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Granite Woods 35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$229,000

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762
Community: Granite Woods
Regency at Wappinger 61 FARMINGTON RD, WAPPINGERS FALLS, NY, ..., Wappingers Falls, NY 12590
$775,000

2 beds

|

2 baths

|

1,738 sq ft

|

House

61 FARMINGTON RD, WAPPINGERS FALLS, NY, ...
Oronoque Village 635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$420,000

1 beds

|

3 baths

|

1,454 sq ft

|

Condo

635 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Hills 656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$634,900

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

656 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 73 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$195,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,731 sq ft

|

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...
Paris Square 5309 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$479,000

1 beds

|

1 baths

|

Condo

5309 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Heritage Village 198 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

198 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Summit at Bethel 12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801
$619,900

2 beds

|

3 baths

|

2,023 sq ft

|

Condo

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...
Oronoque Village 13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

1 beds

|

2 baths

|

1,330 sq ft

|

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 140 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$645,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

140 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
The Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
Heritage Village 423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$320,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$531,500

2 beds

|

3 baths

|

1,590 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Regency at Woodbridge 3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$629,000

3 beds

|

3 baths

|

Condo

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...
Regency at Woodbridge 5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525
$749,000

3 beds

|

3 baths

|

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...
Regency at Woodbridge 5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$649,000

3 beds

|

3 baths

|

Condo

5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
Oronoque Village 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$635,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Heritage Hills 182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$475,000

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$460,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

151 SOUTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winsted, CT? 55places can help!
Questions? Call us: (860) 909-8066
The Retreat at Carmel 4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512
$759,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

4 FROST CT, CARMEL, NY, 10512
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village

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